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Updated: Jun 29, 2025

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
(Indol-3-yl)(DMIX)Iodonium Salts: Novel Electrophilic Indole Reagents
Dmitry I Bugaenko1, Nikolai A Malashchenko1, Sergei O Kopytov1
1Department of Chemistry, Moscow State University, Moscow 119991, Russia.
Abstract:
A new umpolung approach to the C3-H functionalization of indoles with diverse nucleophiles based on the intermediate formation of I(III) reagents is described. The 3,5-dimethylisoxazol-4-yl auxiliary allows for selective indole transfer under catalyst-free conditions, which was impossible using previously reported reagents. Combining the mildness of transition-metal-free conditions and the high reactivity of hypervalent iodine reagents, this protocol tolerates various functional groups and provides access to indoles that are difficult to prepare conventionally.
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